Gil Penchina likes to invest in startup founders that are slightly delusional.That kind of contrarian hunch has propelled Penchina into the super angel bracket, with five $1 billion exits to his name — a high water mark for early stage investing.

Penchina single-handedly built the largest syndicated angel fund with over 500 backers and nearly $5 million per investment. His fund experienced an exit frenzy that includes LinkedIn, Paypal, Wealthfront, Cruise Automation, Dollar Shave Club, and Evite. His own tech and consulting career ranges from bulge bracket startup academies like GE and eBay, running his own shop as CEO of Wikia and co-founder ofFastly.

I caught up with Gil recently (in full disclosure, I invest with Gil) and had the chance to talk to him about the state of the startup ecosystem and his secret formula for knowing if and when a founder has what it takes to go all the way. [ Startup Grind ]